Reductive Umpolung of Carbonyl Derivatives with Visible-Light Photoredox Catalysis: Direct Access to Vicinal Diamines and Amino Alcohols via α-Amino Radicals and Ketyl Radicals

被引：175

作者：

Fava, Eleonora ^{[1
]}

Millet, Anthony ^{[1
]}

Nakajima, Masaki ^{[1
]}

Loescher, Sebastian ^{[1
]}

Rueping, Magnus ^{[1
,2
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr KCC, Thuwal 239556900, Saudi Arabia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 23期

基金：

欧洲研究理事会;

关键词：

amino alcohols; diamines; photocatalysis; redox chemistry; umpolung; C-H BONDS; ALPHA; BETA-UNSATURATED KETONES; ORGANIC-SYNTHESIS; BETA-ACTIVATION; SYNTHETIC APPLICATIONS; MICHAEL ACCEPTORS; MANNICH REACTION; PHOTOCATALYSIS; CYCLIZATION; FUNCTIONALIZATION;

D O I：

10.1002/anie.201511235

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Visible-light-mediated photoredox-catalyzed aldimine-aniline and aldehyde-aniline couplings have been realized. The reductive single electron transfer (SET) umpolung of various carbonyl derivatives enabled the generation of intermediary ketyl and a-amino radical anions, which were utilized for the synthesis of unsymmetrically substituted 1,2-diamines and amino alcohols.

引用

页码：6776 / 6779

页数：4

共 14 条

[1] Accessing α-Amino Ketyl Radicals from β-Amino Alcohols via Chemoselective Hydrogen Atom Transfer Catalysis
Merkens, Kay
Sanosa, Nil
Funes-Ardoiz, Ignacio
Gomez-Suarez, Adrian
ACS CATALYSIS, 2022, 12 (21): : 13186 - 13192
[2] Visible-light promoted photoredox catalysis in flow: addition of biologically important α-amino radicals to michael acceptors
Filipovic, Ana
Dzambaski, Zdravko
Bondzic, Aleksandra M.
Bondzic, Bojan P.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2023, 22 (10) : 2259 - 2270
[3] Visible-light promoted photoredox catalysis in flow: addition of biologically important α‑amino radicals to michael acceptors
Ana Filipović
Zdravko Džambaski
Aleksandra M. Bondžić
Bojan P. Bondžić
Photochemical & Photobiological Sciences, 2023, 22 : 2259 - 2270
[4] Alcohol Etherification via Alkoxy Radicals Generated by Visible-Light Photoredox Catalysis
Rivero, Alexandra R.
Fodran, Peter
Ondrejkova, Alica
Wallentin, Carl-Johan
ORGANIC LETTERS, 2020, 22 (21) : 8436 - 8440
[5] Synthesis of 1,2-amino alcohols by decarboxylative coupling of amino acid derived α-amino radicals to carbonyl compounds via visible-light photocatalyst in water
Pan, Shulei
Jiang, Min
Hu, Jinjin
Xu, Ruigang
Zeng, Xiaofei
Zhong, Guofu
GREEN CHEMISTRY, 2020, 22 (02) : 336 - 341
[6] Direct α-Arylation of α-Amino Carbonyl Compounds with Indoles Using Visible Light Photoredox Catalysis
Wang, Zhi-Qiang
Hu, Ming
Huang, Xiao-Cheng
Gong, Lu-Bing
Xie, Ye-Xiang
Li, Jin-Heng
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19): : 8705 - 8711
[7] Visible Light Photoredox Catalysis: Generation and Addition of N-Aryltetrahydroisoquinoline-Derived α-Amino Radicals to Michael Acceptors
Kohls, Paul
Jadhav, Deepak
Pandey, Ganesh
Reiser, Oliver
ORGANIC LETTERS, 2012, 14 (03) : 672 - 675
[8] 1,6-Addition of Tertiary Carbon Radicals Generated From Alcohols or Carboxylic Acids by Visible-Light Photoredox Catalysis
Abbas, Samir Y.
Zhao, Peng
Overman, Larry E.
ORGANIC LETTERS, 2018, 20 (03) : 868 - 871
[9] Visible-Light Photoredox-Catalyzed Giese Reaction: Decarboxylative Addition of Amino Acid Derived -Amino Radicals to Electron-Deficient Olefins
Millet, Anthony
Lefebvre, Quentin
Rueping, Magnus
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (38) : 13464 - 13468
[10] Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C-O bonds in organic transformations
Roy, Mithu
Sardar, Bitan
Mallick, Itu
Srimani, Dipankar
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2024, 20 : 1348 - 1375

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